In this highly original interdisciplinary study incorporating close readings of literary texts and philosophical argumentation, Henry W. Pickford develops a theory of meaning and expression in art intended to counter the meaning skepticism most commonly associated with the theories of Jacques Derrida.Pickford arrives at his theory by drawing on the writings of Wittgenstein to develop and modify the insights of Tolstoy’s philosophy of art. Pickford shows how Tolstoy’s encounter with Schopenhauer’s thought on the one hand provided support for his ethical views but on the other hand presented a problem, exemplified in the case of music, for his aesthetic theory, a problem that Tolstoy could not successfully resolve. Wittgenstein’s critical appreciation of Tolstoy’s thinking, however, not only recovers its viability but also constructs a formidable position within contemporary debates concerning theories of emotion, ethics, and aesthetic expression.